TWI637958B - 苯并雙(噻二唑)衍生物、含此衍生物之印墨、及使用此衍生物之有機電子元件 - Google Patents
苯并雙(噻二唑)衍生物、含此衍生物之印墨、及使用此衍生物之有機電子元件 Download PDFInfo
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- TWI637958B TWI637958B TW103129981A TW103129981A TWI637958B TW I637958 B TWI637958 B TW I637958B TW 103129981 A TW103129981 A TW 103129981A TW 103129981 A TW103129981 A TW 103129981A TW I637958 B TWI637958 B TW I637958B
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- Prior art keywords
- compound
- organic
- thiadiazole
- substrate
- benzobis
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- 150000004867 thiadiazoles Chemical class 0.000 claims abstract description 77
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 239000004065 semiconductor Substances 0.000 claims description 660
- 239000010410 layer Substances 0.000 claims description 530
- 239000000758 substrate Substances 0.000 claims description 507
- 238000007639 printing Methods 0.000 claims description 161
- 239000010409 thin film Substances 0.000 claims description 51
- 239000000463 material Substances 0.000 claims description 45
- 238000000926 separation method Methods 0.000 claims description 30
- 230000005525 hole transport Effects 0.000 claims description 28
- 239000003960 organic solvent Substances 0.000 claims description 23
- 238000005401 electroluminescence Methods 0.000 claims description 21
- 239000012044 organic layer Substances 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 1010
- 239000010408 film Substances 0.000 description 388
- 230000005669 field effect Effects 0.000 description 281
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 182
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 182
- 230000000704 physical effect Effects 0.000 description 174
- 238000000034 method Methods 0.000 description 173
- 238000005160 1H NMR spectroscopy Methods 0.000 description 166
- 239000000976 ink Substances 0.000 description 157
- 238000004519 manufacturing process Methods 0.000 description 150
- 239000000243 solution Substances 0.000 description 139
- 238000011156 evaluation Methods 0.000 description 138
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 113
- 230000015572 biosynthetic process Effects 0.000 description 108
- 238000004528 spin coating Methods 0.000 description 108
- 238000003786 synthesis reaction Methods 0.000 description 100
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 97
- -1 trifluoromethylphenyl Chemical group 0.000 description 93
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 90
- 238000006243 chemical reaction Methods 0.000 description 82
- 239000004793 Polystyrene Substances 0.000 description 72
- 239000002904 solvent Substances 0.000 description 67
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 64
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 62
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 57
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 57
- 238000003756 stirring Methods 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 52
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 50
- 239000011521 glass Substances 0.000 description 49
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 42
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 229920000642 polymer Polymers 0.000 description 35
- 238000001771 vacuum deposition Methods 0.000 description 35
- 230000000052 comparative effect Effects 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 238000010898 silica gel chromatography Methods 0.000 description 31
- 239000000460 chlorine Substances 0.000 description 29
- 239000000126 substance Substances 0.000 description 29
- 238000000576 coating method Methods 0.000 description 27
- 239000011248 coating agent Substances 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 24
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 23
- RFFLAFLAYFXFSW-RHQRLBAQSA-N 1,2-dichloro-3,4,5,6-tetradeuteriobenzene Chemical compound [2H]C1=C([2H])C([2H])=C(Cl)C(Cl)=C1[2H] RFFLAFLAYFXFSW-RHQRLBAQSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
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- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
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- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 9
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- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 7
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
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- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical class S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- MFRJHJMKJWJZHW-UHFFFAOYSA-N undecane-1-sulfonyl chloride Chemical compound CCCCCCCCCCCS(Cl)(=O)=O MFRJHJMKJWJZHW-UHFFFAOYSA-N 0.000 description 1
- CCIDWXHLGNEQSL-UHFFFAOYSA-N undecane-1-thiol Chemical compound CCCCCCCCCCCS CCIDWXHLGNEQSL-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/52—Electrically conductive inks
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/125—Active-matrix OLED [AMOLED] displays including organic TFTs [OTFT]
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
- H10K10/488—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising a layer of composite material having interpenetrating or embedded materials, e.g. a mixture of donor and acceptor moieties, that form a bulk heterojunction
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K77/00—Constructional details of devices covered by this subclass and not covered by groups H10K10/80, H10K30/80, H10K50/80 or H10K59/80
- H10K77/10—Substrates, e.g. flexible substrates
- H10K77/111—Flexible substrates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Thin Film Transistor (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Electroluminescent Light Sources (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Photovoltaic Devices (AREA)
Applications Claiming Priority (4)
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JP2013-196221 | 2013-09-20 | ||
JP2013196221 | 2013-09-20 | ||
JP2014-026969 | 2014-02-14 | ||
JP2014026969 | 2014-02-14 |
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TW201518305A TW201518305A (zh) | 2015-05-16 |
TWI637958B true TWI637958B (zh) | 2018-10-11 |
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US (1) | US9978954B2 (ja) |
EP (1) | EP3048107B1 (ja) |
JP (1) | JP6427101B2 (ja) |
KR (1) | KR102218514B1 (ja) |
CN (1) | CN105793269B (ja) |
TW (1) | TWI637958B (ja) |
WO (1) | WO2015041026A1 (ja) |
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EP3181569A4 (en) * | 2014-08-13 | 2018-03-21 | UBE Industries, Ltd. | Benzobis(thiadiazole) derivative, ink containing same, and organic electronic device using same |
JP2017025039A (ja) * | 2015-07-27 | 2017-02-02 | 宇部興産株式会社 | 膜中で特定の結晶構造を有するベンゾビス(チアジアゾール)誘導体の結晶、その結晶の膜、及びそれを用いた有機エレクトロニクスデバイス |
JP2017025047A (ja) * | 2015-07-28 | 2017-02-02 | 宇部興産株式会社 | ベンゾビス(チアジアゾール)誘導体、それを含むインク、及びそれを用いた有機エレクトロニクスデバイス |
GB2547460A (en) * | 2016-02-19 | 2017-08-23 | Cambridge Display Tech Ltd | Solvent systems for tuning of the external quantum efficiency of organic photodiodes |
WO2017190345A1 (en) * | 2016-05-06 | 2017-11-09 | South University Of Science And Technology Of China | Molecular fluorophores and preparation method thereof and use for short wavelength infrared imaging |
EP3487955B1 (en) * | 2016-07-19 | 2020-05-20 | Merck Patent GmbH | Liquid crystalline medium |
CN109384801B (zh) * | 2017-08-10 | 2022-08-09 | 松下知识产权经营株式会社 | 光电转换材料以及光电转换元件 |
WO2019238567A1 (en) | 2018-06-11 | 2019-12-19 | Merck Patent Gmbh | Liquid crystalline medium |
JP7391888B2 (ja) * | 2018-06-20 | 2023-12-05 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 液晶媒体 |
CN110505767B (zh) * | 2019-07-08 | 2021-03-30 | 苏州固泰新材股份有限公司 | 一种软性铜箔基材及其制备方法 |
CN110330519B (zh) * | 2019-07-25 | 2020-09-22 | 中国科学院长春应用化学研究所 | 基于硼氮配位键的n-型有机半导体材料及其制备方法与应用 |
CN112337445A (zh) * | 2020-10-16 | 2021-02-09 | 邓颖菁 | 一种吸附重金属的纳米聚酯膜及其制备方法 |
CN114057774A (zh) * | 2021-12-06 | 2022-02-18 | 电子科技大学 | 含噻吩并噻二唑结构的有机光电分子材料及其制备方法和应用 |
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US20060052612A1 (en) * | 2002-06-29 | 2006-03-09 | Covion Organic Semiconductors Gmbh Intellectual Property Group | 2,1,3-Benothiadiazoles for use as electronic active components |
JP2013124231A (ja) * | 2011-12-14 | 2013-06-24 | Nippon Shokubai Co Ltd | ベンゾビスチアジアゾール化合物 |
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US4885211A (en) | 1987-02-11 | 1989-12-05 | Eastman Kodak Company | Electroluminescent device with improved cathode |
JP3236332B2 (ja) | 1991-01-29 | 2001-12-10 | パイオニア株式会社 | 有機エレクトロルミネッセンス素子 |
JP4281320B2 (ja) | 2002-10-15 | 2009-06-17 | 凸版印刷株式会社 | 有機薄膜トランジスタの製造方法 |
JP2006206503A (ja) | 2005-01-28 | 2006-08-10 | Tokyo Institute Of Technology | π電子系化合物、及びそれを用いたn−型有機電界効果トランジスタ |
KR100914383B1 (ko) * | 2006-06-20 | 2009-08-28 | 주식회사 엘지화학 | 폴리헤테로고리 화합물, 이를 이용한 유기 전자 소자 및 이유기 전자 소자를 포함하는 전자 장치 |
JP5209996B2 (ja) * | 2007-03-23 | 2013-06-12 | 山本化成株式会社 | 有機トランジスタ |
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2014
- 2014-08-29 CN CN201480063334.1A patent/CN105793269B/zh not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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TW201518305A (zh) | 2015-05-16 |
JP6427101B2 (ja) | 2018-11-21 |
EP3048107A1 (en) | 2016-07-27 |
KR102218514B1 (ko) | 2021-02-19 |
US20160276598A1 (en) | 2016-09-22 |
CN105793269B (zh) | 2018-01-09 |
EP3048107B1 (en) | 2021-01-13 |
EP3048107A4 (en) | 2017-05-31 |
JPWO2015041026A1 (ja) | 2017-03-02 |
CN105793269A (zh) | 2016-07-20 |
KR20160055927A (ko) | 2016-05-18 |
US9978954B2 (en) | 2018-05-22 |
WO2015041026A1 (ja) | 2015-03-26 |
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